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AI Strategist, Senior Director

Chicago, IL 1 day ago ✦ New

Job Description

AI Strategist

Senior Director, Consulting & Delivery


Level & Department

The honest version of what's happening in enterprise AI in the middle market ($100M - $2B) right now is messy. Most organizations know they need to move. Very few have the leadership that can operate fluently at both ends of the problem… the C-suite conversation about investment rationale and the engineering conversation about whether the architecture can actually support what was just promised.


That gap is expensive and we've seen it in every sector we work in. It shows up the same way every time: smart strategy work that doesn't connect to anything deployable, or capable technical teams building things that never get funded or adopted.


The Principal AI Strategist role exists to close that gap on our most important engagements.


THE ROLE

What this position actually does

You are the senior-most strategy and delivery mind on a client engagement. You hold the intellectual and commercial thread across the entire lifecycle from the first diagnostic conversation through to a working AI system in production and the expansion that follows when the client realizes it's changing something real.


You are not the person who manages the team to do the thinking… you are responsible for the most strategic form of that thinking. You shape the strategy, challenge the architecture, own the executive relationship, and are personally accountable for whether the engagement creates measurable business value.


The title is Principal AI Strategist because that's the actual job. The level is Senior Director because that reflects the scope, accountability, and authority this role carries inside Quantum Rise and in front of clients.



OUR OPERATING PRINCIPLES

The intellectual framework you'll work inside

Quantum Rise operates from a set of principles we call Consulting 2.0. They define how engagements are structured, how we challenge client assumptions, and what we hold ourselves accountable to.


Think like an investor, not a technologist

AI value is relative to each client’s own goals / circumstances and capital is precious. We anchor every engagement to strategy → value streams → enterprise value. We don't start with use cases. We start with where the business makes and loses money, and work backward to where AI creates leverage.

  • Map to where the work actually happens: We go to L4–L5 process depth where the task-level execution that explains KPI performance and reveals where AI readiness actually exists.
  • Diagnose before prescribing: We use structured diagnostic lenses (process, data, systems) to move from visible symptoms to root causes.
  • Data reality bounds AI ambition: What AI can reliably do is determined by the strength of the data foundation (architecture, integration, quality, consumption) not by model choice.
  • Not all AI systems are created equal: Machine learning, LLMs, and agents introduce different capabilities, constraints, and operational trade-offs. Enterprise-ready agents specifically require probabilistic reasoning balanced with deterministic rules, structure, guardrails, and human oversight.
  • Risk is predictable: Enterprise AI risk falls into defined categories: data privacy, bias, explainability, and governance. Principles define what good looks like; governance establishes ownership, decision rights, and escalation.
  • Execution credibility matters as much as technical ambition: “Crawl”and MVP solutions that are in production beat “Run” enterprise-wide solutions that aren't.


RESPONSIBILITIES

What you own

Client strategy and delivery

  • Lead end-to-end engagement execution from strategy and diagnostic through deployment and commercial expansion
  • Run executive discovery sessions translating ambiguous business problems into structured AI investment rationales
  • Build the business case with the rigor of an investor, not the optimism of a vendor: quantified value, honest constraints, sequenced roadmap
  • Own the relationship with C-suite and senior client stakeholders as a peer, not a service provider

Technical leadership

  • Apply working fluency in LLMs, agentic workflows, RAG architecture, and data infrastructure to make real design decisions ensuring the original business value is obtained
  • Collaborate with engineering to challenge, refine, and pressure-test solutions against production realities
  • Define AI product roadmaps that are incrementally value generating, governed, measured, and adopted

Firm development

  • Identify capability and offering gaps where Quantum Rise can build durable competitive advantage
  • Build reusable delivery IP (frameworks, playbooks, diagnostic tools) that improve every engagement that follows
  • Develop and mentor the next generation of AI consultants on what it means to operate at the intersection of AI strategy and delivery
  • Contribute to business development through the quality of your work and the depth of your client relationships


THE PROFILE

Who fits here

person who thrives in this role has a particular combination that's genuinely rare and we'd rather name it honestly than let both sides waste time discovering the mismatch.


Dimension: What this looks like in practice

Role identity: You think of yourself as a strategist who builds things, not a consultant who advises on them.


Technical depth: Hands-on with LLMs and agentic coding. You've debugged a pipeline at some point and don't need to be reminded why hallucination is an enterprise risk.


Business fluency: You can translate AI capability into a CFO-ready investment case without losing the technical precision that makes it credible.


Delivery record: 12+ years in management consulting or technical advisory with real end-to-end accountability from scoping through go-live. You are hyper customer service oriented.


Sector context: You have meaningfully operated across 3 discrete sectors learning to how effectively understand how money is actually made, customer and demand dynamics, how work gets done, regulatory constraints, etc.


Education: Engineering, CS, or MIS undergraduate foundation. MBA preferred. The combination matters and what makes the translation instinct natural. What matters is the ability to translate value creation into technology and vice versa.


Working style: You reach for the AI tool first because it's genuinely how you think and not just because we’re an AI consultancy.


BENEFITS

What we offer

  • Competitive base salary + variable compensation tied to individual and company performance
  • Equity options
  • BCBS health, vision, and dental
  • 401(k) with discretionary annual match
  • FSA, DCA, commuter, and L&D stipends
  • Unlimited PTO + paid holidays + paid sick time

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